CH233084A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH233084A CH233084A CH233084DA CH233084A CH 233084 A CH233084 A CH 233084A CH 233084D A CH233084D A CH 233084DA CH 233084 A CH233084 A CH 233084A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- dye
- disazo dye
- parts
- dioxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/18—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
Terfahren zur Herstellung eines Msazofäarbstoffes. Es wurde gefunden, dass ein wertvoller Disazofarbstoff hergestellt werden kann. wenn man tetrazotiertes 3. 3'-Dioxy-4. 4'-di- aminodiphenyl beidseitig mit 1-(4'-ss-Oxy- äthoxyphenyl)-3-methyl-5-pyrazo1onkuppelt.
Der neue Farbstoff ist ein dunkles Pul ver und färbt pflanzliche Fasern nach dem ein- oder zweibädigen Nachkupferungsver- fahren in wasch- und lichtechten bordeaux roten Tönen. Die Tetrazotierung des 3 . 3'-Dioxy-4 . 4'- diaminodiphenyls, das zum Beispiel durch Verseifung von Dianisidin mit Aluminium chlorid erhalten werden kann, erfolgt in übli cher Weise:
Das 1-(4'-ss-Oxyäthoxyphenyl)- a-methyl-5-pyrazolon kann nach der norma lerweise zur Herstellung von Pyrazolonen,ver- wendeten Methode, z. B. ausgehend von 1 Amino-4-(ss-oxyäthoxy)-benzol der Formel
EMI0001.0024
erhalten werden. Die Kupplung wird in alka- lischer, beispielsweise Alkalicarbonat oder Alkalihydroxy d enthaltender Lösung vor genommen.
<I>Beispiel:</I> Zu einer Lösung von 4,32 Teilen 3 . 3'-Di- oxy-4. 4'-diaminodiphenyl in einem Gemisch von 10 Raumteilen 30%iger Salzsäure und 200 Teilen Wasser wird eine wässerige Lö sung von 2,76 Teilen Natriumnitrit gegeben. Die Tetrazotierung erfolgt sofort.
In 200 Tei len Wasser werden unter Zusatz von 30 Raumteilen" 30 % iger Natronlauge 9,36 Teile 1- (4' -,8- Oxyäthoxy -phenyl)-3-methyl-5-pyr- " azolon und 20 Teile wasserfreies Natriümcar- bonat gelöst.
Zu dieser Mischung gibt man bei 10 bis 15 die wie oben angegeben berei tete Tetrazolösung zu. und rührt 24 Stunden bei Zimmertemperatur. Dann wird die alka lische Reaktion des Kupplungsgemisches mit 30%iger Salzsäure abgestumpft und der Farbstoff durch Zusatz von Kochsalz abge schieden, abfiltriert und getrocknet.
A method for the preparation of a mazo dye. It has been found that a valuable disazo dye can be produced. if one tetrazotized 3. 3'-dioxy-4. 4'-diaminodiphenyl coupled with 1- (4'-ss-oxyethoxyphenyl) -3-methyl-5-pyrazolone on both sides.
The new dye is a dark powder and colors vegetable fibers using the one- or two-bath re-coppering process in washable and lightfast burgundy red tones. The tetrazotization of the 3rd 3'-dioxy-4. 4'-diaminodiphenyls, which can be obtained, for example, by saponifying dianisidine with aluminum chloride, takes place in the usual way:
The 1- (4'-ss-Oxyäthoxyphenyl) - a-methyl-5-pyrazolon can according to the normally for the production of pyrazolones, used method, z. B. starting from 1 amino-4- (ss-oxyethoxy) benzene of the formula
EMI0001.0024
can be obtained. The coupling is carried out in an alkaline solution, for example containing alkali carbonate or alkali hydroxide.
<I> Example: </I> For a solution of 4.32 parts 3. 3'-dioxy-4. 4'-diaminodiphenyl in a mixture of 10 parts by volume of 30% strength hydrochloric acid and 200 parts of water is given an aqueous solution of 2.76 parts of sodium nitrite. Tetrazotization takes place immediately.
In 200 Tei len water with the addition of 30 parts by volume "30% sodium hydroxide solution 9.36 parts 1- (4 '-, 8-oxyethoxy-phenyl) -3-methyl-5-pyr-" azolone and 20 parts of anhydrous sodium car- bonat solved.
The tetrazo solution prepared as indicated above is added to this mixture at 10-15. and stir for 24 hours at room temperature. Then the alkaline reaction of the coupling mixture is truncated with 30% hydrochloric acid and the dye is deposited by adding sodium chloride, filtered off and dried.
Claims (1)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH233084T | 1941-02-18 | ||
| CH232505T | 1941-02-18 | ||
| CH609299X | 1942-02-03 | ||
| CH616155X | 1942-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233084A true CH233084A (en) | 1944-06-30 |
Family
ID=27429730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233084D CH233084A (en) | 1941-02-18 | 1941-02-18 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH233084A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476261A (en) * | 1946-04-11 | 1949-07-12 | Ciba Ltd | Process for the manufacture of asymmetrical polyazo-dyestuffs |
-
1941
- 1941-02-18 CH CH233084D patent/CH233084A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476261A (en) * | 1946-04-11 | 1949-07-12 | Ciba Ltd | Process for the manufacture of asymmetrical polyazo-dyestuffs |
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